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Intramolecular and Ferrier Rearrangement Strategy for the Construction of C1‐ β ‐ d ‐xylopyranosides: Synthesis, Mechanism and Biological Activity Study
Author(s) -
Yao Yuan,
Xiong CaiPing,
Zhong YaLing,
Bian GuoWei,
Huang NianYu,
Wang Long,
Zou Kun
Publication year - 2019
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201801423
Subject(s) - chemistry , intramolecular force , circular dichroism , electrospray ionization , stereochemistry , nuclear magnetic resonance spectroscopy , two dimensional nuclear magnetic resonance spectroscopy , proton nmr , molecule , mass spectrometry , organic chemistry , chromatography
A stereoselective synthesis of C1‐ β ‐ d ‐xylopyranoside derivatives had been developed via intramolecular 1,3‐acyloxy migration/Ferrier rearrangement stategy from readily available propargylic carboxylates and d ‐xylal. A combined catalytic system of chloro(triphenylphosphine)gold(I) (Ph 3 PAuCl) and silver hexafluoroantimonate (AgSbF 6 ) was found to possess the most effective of the reaction, and 20 examples tested the wide functional compatibility for these transformation. Nuclear magnetic resonance (NMR), infrared spectrum (IR), high resolution electrospray ionization mass spectroscopy (HRESIMS) and isotopic labelling experiments were utilized to investigate the C1‐glycosylation process. The relative configuration for the products was determined by two‐dimensional (2D) NMR NMR and electronic circular dichroism spectroscopy. 3‐(4,5)‐Dimethylthiahiazo(‐z‐y1)‐3,5‐diphenytetrazoliumro‐mide (MTT) cell viability assays indicated that three of them showed strong anti‐proliferative activities against human gastric cancer HGC‐27 cells with IC 50 values of 17.09‐38.88 μM. This method opened up new horizons for the synthesis of bioactive C‐glycosylated molecules.